US4317816A - Saponin containing composition effective against adrenal atrophy - Google Patents

Saponin containing composition effective against adrenal atrophy Download PDF

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Publication number
US4317816A
US4317816A US06/172,006 US17200680A US4317816A US 4317816 A US4317816 A US 4317816A US 17200680 A US17200680 A US 17200680A US 4317816 A US4317816 A US 4317816A
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Prior art keywords
glucopyranosyl
saponin
group
adrenal atrophy
administering
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US06/172,006
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English (en)
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Shigeru Arichi
Yoshihiro Uchida
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Osaka Chemical Laboratory Co Ltd
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Osaka Chemical Laboratory Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J17/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, having an oxygen-containing hetero ring not condensed with the cyclopenta(a)hydrophenanthrene skeleton
    • C07J17/005—Glycosides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/185—Magnoliopsida (dicotyledons)
    • A61K36/25—Araliaceae (Ginseng family), e.g. ivy, aralia, schefflera or tetrapanax
    • A61K36/258—Panax (ginseng)
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P5/00—Drugs for disorders of the endocrine system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P5/00—Drugs for disorders of the endocrine system
    • A61P5/38—Drugs for disorders of the endocrine system of the suprarenal hormones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/20—Carbocyclic rings
    • C07H15/24—Condensed ring systems having three or more rings
    • C07H15/256—Polyterpene radicals

Definitions

  • This invention relates to a pharmaceutical composition containing saponin from medicinal ginseng, which is useful for the treatment and prevention of trouble which is due to glucocorticoids belonging to adrenocortical hormones.
  • glucocorticoids belonging to adrenocortical hormones such as cortisone
  • cortisone provide an indispensable medicine which protects a living body from stress, and takes part in conversion of proteins to glucides, metabolism of lipids, or the like.
  • Cushing's syndrome including abnormal fat deposition and edema in the face, neck or body, such as moon face and buffalo neck, abnormal increase of appetite, increase of body weight, pigmentation of the skin and nails, skin keratinization, hyperglycemia, hypertension, muscle force reduction, hypokalemia, and worsening of the existing ulcer. They also cause serious trouble to the organs, such as atrophy of adrenal cortex.
  • the saponins of medicinal ginsengs effectively act against the atrophy of the adrenal due to glucocorticoids and the accompanying reduction of plasma cortisol. They are useful for the treatment of the adrenal atrophy, and effective against the side effects associated therewith.
  • the mechanism of their action against burns has not yet been clarified, but their use in combination with glucocorticoids has shown a clear synergistic effect which has not been achieved by glucocorticoids alone.
  • a pharmaceutical composition comprising a glucocorticoid and a saponin from medicinal ginseng, which acts against the side effects of glucocorticoids, and a medicine for glucocorticoids containing a saponin of medicinal ginseng, which is useful for the prevention and treatment of adrenal atrophy, and any other trouble in the organs.
  • Panax ginseng C. A. Meyer is the most preferred ginseng containing saponin for the purposes of this invention. Other ginsengs of the same family may, however, be used. They include Panax japonicus C. A. Meyer, Panax quinquefolium LINNE, Panax pseudo-ginseng WALICH, and Panax notoginseng BURKILL.
  • saponin by preparing a crude drug from any of the aforementioned ginsengs, extracting the saponin from it, and refining it, or by the tissue culture of a piece of rhizome cut from ginseng, followed by the extraction and purification of the saponin therefrom.
  • saponin as herein used means a mixture obtained by any such method, and consisting substantially of saponins.
  • the saponin can, for example, be obtained from a crude drug of ginseng in the following way.
  • the active constituent of ginseng is extracted with water, a lower aliphatic alcohol, or a lower aliphatic alcohol containing water, and concentrated by evaporation to form an extract of ginseng.
  • the ginseng used for this purpose may be defatted with an ordinary fat-soluble organic solvent, if required.
  • the extract is dissolved in n-butanol, and water is added into the solution with a shake. After the solution is left stationary to separate the insoluble matter, the n-butanol layer is dried by evaporation.
  • the residue is dissolved in a lower aliphatic alcohol, and the solution is injected into ether with stirring. The precipitate thereby formed is collected by filtration. See Japanese Patent Publication No. 5016/1973.
  • the extract thus obtained consists substantially of saponin, and can directly be used as an active constituent for the composition according to this invention.
  • the saponin contains the compounds of formulas (I), (II), and (III), which will hereinafter be described in detail, though the kind and quantity of its components may somewhat differ with the kind of the ginseng employed and its age of cultivation.
  • the saponin is a yellow white or brown, bitter powder which is easily soluble in water, methanol and dilute methanol, soluble in ethanol, and insoluble in chloroform, ether and carbon tetrachloride.
  • the acid hydrolysis of the saponin yields anhydrous dextrose from its water soluble portion, and panaxadiol (C 30 H 52 O 3 ) having a melting point of 205° C. and/or panaxatriol (C 30 H 52 O 4 ) having a melting point of 238° C. to 239° C. from its water insoluble portion.
  • the saponin may also be obtained by tissue culture, for example, in the following way.
  • a tissue slice of ginseng rhizome is placed in a culture medium composed of 500 ml of the Knop liquid medium containing 1,000 mg of calcium sulfate, 250 mg of potassium nitrate, 250 mg of magnesium sulfate and 250 mg of potassium phosphate, per liter, 1 ml/lit. of d'Heller's mineral solution, 5% of anhydrous dextrose, 10 -6 g of vitamin B, 10 -6 g of biotin, 10 -6 g of kinetin and 1% of agar, and is maintained at 26° C. for culture and growth, whereby a ginseng callus is obtained.
  • the callus is increased in the same culture medium, and the saponin is extracted and purified as described before.
  • the saponin contains at least one of the ginsenosides represented by formulas (I) and (II) below, and may also in some cases contain ⁇ -D-glucopyranosyloleanate-(3)- ⁇ -D-glucopyranosyl(1 ⁇ 2)-.beta.-D-glucuronopyranosido represented by formula (III).
  • Formula I is represented by the following: ##STR1## wherein R 1 represents a ⁇ -D-glucopyranosyl(1 ⁇ 2)- ⁇ -D-glucopyranosyl group, and R 2 represents a ⁇ -D-glucopyranosyl(1 ⁇ 6)- ⁇ -D-glucopyranosyl, ⁇ -L-arabinopyranosyl(1 ⁇ 6)- ⁇ -D-glucopyranosyl, ⁇ -D-xylopyranosyl(1 ⁇ 6)- ⁇ -D-glucopyranosyl, ⁇ -L-arabinofuranosyl(1 ⁇ 6)- ⁇ -D-glucopyranosyl or ⁇ -D-glucopyranosyl group.
  • Formula II is represented by the following: ##STR2## wherein R 3 represents an ⁇ -L-rhamnopyranosyl(1 ⁇ 2)- ⁇ -D-glucopyranosyl, ⁇ -D-glucopyranosyl(1 ⁇ 2)- ⁇ -D-glucopyranosyl, ⁇ -D-glucopyranosyl or ⁇ -L-rhamnopyranosyl(1 ⁇ 2)- ⁇ -D-glucopyranosyl group, and R 4 represents a hydrogen atom or a ⁇ -D-glucopyranosyl group.
  • Formula III is represented by the following: ##STR3## wherein R 5 represents a ⁇ -D-glucopyranosyl group, and R 6 represents a ⁇ -D-glucopyranosyl(1 ⁇ 2)- ⁇ -D-glucuronopyranosyl group.
  • the saponin represented by formula (I) or (II) is a saponin belonging to the dammarane glycosides of triterpenes.
  • the saponins of formulas (I) and (II) are presently found solely in medicinal ginseng.
  • the compounds represented by formula (I) include 20S-protopanaxadiol-3-[O- ⁇ -D-glucopyranosyl(1 ⁇ 2)- ⁇ -D-glucopyranosido]-20-[O- ⁇ -D-glucopyranosyl(1 ⁇ 6)- ⁇ -D-glucopyranosido] (ginsenoside Rb 1 ), 20S-protopanaxadiol-3-[O- ⁇ -D-glucopyranosyl(1 ⁇ 2)- ⁇ -D-glucopyanosido]-20-[O- ⁇ -L-arabinopyranosyl(1 ⁇ 6)- ⁇ -D-glucopyranosido] (ginsenoside Rb 2 ), 20S-protopanaxadiol-3-[O- ⁇ -D-glucopyranosyl(1 ⁇ 2)- ⁇ -D-glucopyranosido]-20-[O- ⁇ -L-arabinofuranos
  • the compounds represented by formula (II) include 20-8-protopanaxatriol-6-[O- ⁇ -L-rhamnopyranosyl(1 ⁇ 2)- ⁇ -D-glucopyranosido]-20-O- ⁇ -D-glucopyranosido (ginsenoside Re), 20S-protopanaxatriol-6-O- ⁇ -D-glucopyranosyl(1 ⁇ 2)- ⁇ -D-glucopyranosido (ginsenoside Rf), 20S-protopanaxatriol-6-,20-di-O- ⁇ -D-glucopyranosido (ginsenoside Rg 1 ), 20S-protopanaxatriol-6-O- ⁇ -L-rhamnopyranosyl(1 ⁇ 2)- ⁇ -D-glucopyranosido (ginsenoside Rg 2 ), 20S-protopanaxatriol-6-[O- ⁇ -D-glucopyranosyl(1 ⁇
  • Panax ginseng C. A. MEYER contains a saponin having an unknown structure, but considered to have a skeleton similar to that of formula (I). It is called ginsenoside Ra, and belongs to the saponins for the purpose of this invention. See Chem. Pharm. Bull., 22(2), pages 421-428 (1974), and the Journal of Pharmacy, 94(2), pages 252-260 (1974).
  • the aforementioned individual compounds can be obtained if the saponin obtained as hereinbefore described is divided and purified, for example, by silica gel column chromatography or high speed liquid chromatography with a developing solvent composed of chloroform, methanol and water, or n-butanol, acetic acid and water. It is, however, economically advisable to use a mixture of the compounds, rather than dividing it into the individual saponins.
  • Glucocorticoids belong to the adrenocortical hormones, and specifically include cortisone, hydrocortisone, corticosterone, prednisone prednisolone, methyl prednisolone, triamcinolone, dexamethasone, paramethasone and betamethasone, and their acetate, succinate, phosphate and sulfate, and alkali metal salts of said succinate, phosphate and sulfate.
  • the dosage of the saponin according to this invention depends on the condition of a disease, but is generally 5 to 500 mg, preferably 10 to 250 mg, in three or four doses a day for internal use on an adult.
  • the dosage of the glucocorticoid depends on the kind of the compound used, and the condition of a disease.
  • Acetate cortisone which is a typical example of the glucocorticoids, is dosed in the amount of 5 to 30 mg a day, though as much as 200 to 400 mg a day may be used for the initial treatment of an actute disease.
  • saponin and the glucocorticoid are used together.
  • any known dosage form may be employed for the glucocorticoids, whether it may be for oral or parenteral administration.
  • Examples of the dosage form for oral administration include tablets, powders, stock powders, granules, suspensions and lemonades.
  • Examples of the dosage form for parenteral administration include injections, ointments, emulsions, pastes, poultices, and aerosols.
  • a preparation for oral administration should preferably contain 5 to 100 mg of saponin and 0.5 to 10 mg of glucocorticoid per gram or tablet.
  • a parenteral preparation for external use should preferably contain 0.1 to 10% (w/v) of saponin and 0.05 to 1% (w/v) of glucocorticoid.
  • An injection should preferably contain 5 to 50 mg of saponin and 1 to 25 mg of glucocorticoid per milliliter.
  • saponin alone its dosage form may be chosen from among powders, tablets, injections, ointments, or the like. It can be formed into any such form of preparation.
  • compositions may be produced by any method well known in the art, using excipients and various kinds of additives appropriately selected from among those known in the art.
  • the toxicity of the saponin is so low that it has shown a LD 50 of 637 mg/kg when administered intraperitoneally into mice. Therefore, an adequate daily dosage of saponin does not produce any side effect on a human body.
  • the water saturated n-butanol layer was separated, and dried by vacuum distillation at a temperature not higher than 80° C.
  • the residue obtained was dissolved in 3 liters of methanol, and the solution was injected into 60 liters of ether under stirring. After the solution was left for one day as it was, the precipitate formed was collected by filtration, and dried under reduced pressure at a temperature not higher than 60° C., whereby 260 g of saponin were obtained.
  • 100 g of this saponin was subjected to silica gel column chromatography with a developing agent composed of n-butanol, acetic acid and water, whereby ginsenosides Rb 1 and Rg 1 were isolated.
  • the saponins were tested for their effects on the adrenal atrophy and the blood plasma cortisole, as follows:
  • the administration of the saponins was started on the 11th day.
  • 10 mg/kg of ginseng saponin, 2 mg/kg of ginsenoside Rb 1 and 2 mg/kg of ginsenoside Rg 1 were intraperitoneally administered every day for 10 days into the rats of the respective groups.
  • 1 ml/kg of a physiological saline solution was intraperitoneally administered for 10 days beginning on the 11th day. Then, the rats were abdominally cut, and the adrenal weight and the amount of the plasma cortisone were measured for each group of rats.
  • the results were as follows:
  • the saponin and its constituents are all markedly effective against the reduction in the weight due to the adrenal atrophy, and in the amount of plasma control. As described at B, they were also effective when administered prior to the glucocorticoid. Thus, the saponin and its constituents are useful for both treatment and prevention of diseases.
  • a 59-year-old woman whose case was diagnosed as chronic nephritis five years ago, started to take predonisolone two years ago, and had a buffalo neck during the fourth month thereafter. Accordingly, she started to take a powder containing 5 mg of prednisolone and 100 mg of saponin twice a day in the morning and the evening. Then, her buffalo neck was gradually improved, and after three months, her neck became distinguishable from the upper parts of her shoulders. She continued to take the powder for another three months, and her edema, languor, or the like disappeared.
  • a 32-year-old man whose case was diagnosed as chronic rheumatic arthritis, did not take any adrenocortical hormone. He took a powder containing 5 mg of prednisolone and 10 mg of saponin every day in the morning and the evening. After four months, the serious pain, edema and motor disturbance on his knee joints were completely improved without any side effect of steroid.

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  • Health & Medical Sciences (AREA)
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  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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US06/172,006 1979-08-13 1980-07-24 Saponin containing composition effective against adrenal atrophy Expired - Lifetime US4317816A (en)

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JP10333679A JPS5626818A (en) 1979-08-13 1979-08-13 Glucocorticoid drug
JP54-103336 1979-08-13

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JP (1) JPS5626818A (enrdf_load_stackoverflow)
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DE (1) DE3029363A1 (enrdf_load_stackoverflow)
GB (1) GB2056855B (enrdf_load_stackoverflow)

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4684628A (en) * 1985-05-03 1987-08-04 Yaguang Liu Pharmaceutical composition containing pure San-Mai-Sen
WO1990008315A1 (en) * 1989-01-13 1990-07-26 Pang Peter K T Composition and method for treatment of senile dementia
US5318906A (en) * 1991-06-05 1994-06-07 Nippon Oil Company, Ltd. Agent for stimulating growth of animal cells and serum-free medium containing same
US5397778A (en) * 1994-02-25 1995-03-14 New England Deaconess Hospital Corporation Enteral formulations for treatment of inflammation and infection
US5455232A (en) * 1992-02-04 1995-10-03 Piljac; Goran Pharmaceutical preparation based on rhamnolipid
US5747538A (en) * 1994-03-18 1998-05-05 L.V.M.H. Recherche Use of ginsenoside R0 or a plant extract containing same to promote collagen synthesis
US5762935A (en) * 1994-02-25 1998-06-09 Beth Israel Deaconess Medical Center, Inc. Anti-inflammatory and infection protective effects of sesamin-based lignans
US5776463A (en) * 1997-02-19 1998-07-07 Arginteanu; Ronit Method of reducing stress and circulatory heart disease with freeze-dried borage petal extracts
WO2000023090A1 (en) * 1998-10-21 2000-04-27 Hauser, Inc. Process for removing impurities from natural product extracts
US20030104079A1 (en) * 2000-05-31 2003-06-05 Japan Science And Technology Corporation, Japan Skin tissue regeneration promoters comprising ginsenoside Rb1
WO2005023281A1 (en) * 2003-09-06 2005-03-17 Oscotec Inc. Composition comprising notoginseng radix extract for preventing and treating arthritis as an effective ingredient
US6897298B2 (en) * 2000-01-03 2005-05-24 Guangdong Taihe Biopharmaceutical Co., Ltd. Method for extracting a compound from a ginseng spp. plant, ginseng or pseudo-ginseng
US20050232908A1 (en) * 2002-04-08 2005-10-20 Dong-Hyun Kim Novel use of the extract of processed ginseng and saponin isolated therefrom
US6962719B1 (en) * 2000-01-11 2005-11-08 Pharmaceutical Industry Technology And Development Center Anti-ulcer pharmaceutical composition and the preparation thereof
US8927033B2 (en) 2009-12-21 2015-01-06 Lion Corporation Hyperlipemia-ameliorating agent, anemia-ameliorating composition, uric-acid-level-reducing composition, and food or beverage

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5849314A (ja) * 1981-09-18 1983-03-23 Yamanouchi Pharmaceut Co Ltd 抗副腎皮質機能低下症剤
JPS5936621A (ja) * 1982-08-25 1984-02-28 Tsumura Juntendo Inc 脂肪分解促進作用阻害剤
CH661443A5 (en) * 1984-11-22 1987-07-31 Seuref Ag Pharmaceutical compositions having metabolic activity
US4755504A (en) * 1985-10-03 1988-07-05 Yaguang Liu Pharmaceutical composition from Tienchi
CN111235124B (zh) * 2020-01-19 2023-04-07 云南农业大学 珠子参糖基转移酶UGTPjm2及其在制备竹节参皂苷IVa上的应用

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3284304A (en) * 1961-06-21 1966-11-08 Applic Chimiques Soc D Compositions and methods of using corticosteroids and thiamine derivatives
US4157894A (en) * 1976-06-03 1979-06-12 Inverni Della Beffa S.P.A. Production and analysis of ginseng root extract

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3284304A (en) * 1961-06-21 1966-11-08 Applic Chimiques Soc D Compositions and methods of using corticosteroids and thiamine derivatives
US4157894A (en) * 1976-06-03 1979-06-12 Inverni Della Beffa S.P.A. Production and analysis of ginseng root extract

Cited By (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4684628A (en) * 1985-05-03 1987-08-04 Yaguang Liu Pharmaceutical composition containing pure San-Mai-Sen
WO1990008315A1 (en) * 1989-01-13 1990-07-26 Pang Peter K T Composition and method for treatment of senile dementia
US4966893A (en) * 1989-01-13 1990-10-30 Pang Peter K T Method for treatment of senile dementia
US5137878A (en) * 1989-01-13 1992-08-11 Pang Peter K T Composition and method for treatment of senile dementia
US5318906A (en) * 1991-06-05 1994-06-07 Nippon Oil Company, Ltd. Agent for stimulating growth of animal cells and serum-free medium containing same
US5455232A (en) * 1992-02-04 1995-10-03 Piljac; Goran Pharmaceutical preparation based on rhamnolipid
US5397778A (en) * 1994-02-25 1995-03-14 New England Deaconess Hospital Corporation Enteral formulations for treatment of inflammation and infection
US5674853A (en) * 1994-02-25 1997-10-07 Beth Israel Deaconess Medical Center, Inc. Enternal formulations for treatment of inflammation and infection
US5762935A (en) * 1994-02-25 1998-06-09 Beth Israel Deaconess Medical Center, Inc. Anti-inflammatory and infection protective effects of sesamin-based lignans
US5747538A (en) * 1994-03-18 1998-05-05 L.V.M.H. Recherche Use of ginsenoside R0 or a plant extract containing same to promote collagen synthesis
US5776463A (en) * 1997-02-19 1998-07-07 Arginteanu; Ronit Method of reducing stress and circulatory heart disease with freeze-dried borage petal extracts
WO2000023090A1 (en) * 1998-10-21 2000-04-27 Hauser, Inc. Process for removing impurities from natural product extracts
US6132726A (en) * 1998-10-21 2000-10-17 Hauser, Inc. Process for removing impurities from natural product extracts
US6897298B2 (en) * 2000-01-03 2005-05-24 Guangdong Taihe Biopharmaceutical Co., Ltd. Method for extracting a compound from a ginseng spp. plant, ginseng or pseudo-ginseng
US6962719B1 (en) * 2000-01-11 2005-11-08 Pharmaceutical Industry Technology And Development Center Anti-ulcer pharmaceutical composition and the preparation thereof
US20030104079A1 (en) * 2000-05-31 2003-06-05 Japan Science And Technology Corporation, Japan Skin tissue regeneration promoters comprising ginsenoside Rb1
US20060240129A1 (en) * 2000-05-31 2006-10-26 Japan Science And Technology Corporation Skin tissue regeneration promoters comprising ginsenoside Rb1
US20050232908A1 (en) * 2002-04-08 2005-10-20 Dong-Hyun Kim Novel use of the extract of processed ginseng and saponin isolated therefrom
US7645465B2 (en) 2002-04-08 2010-01-12 Kuan Industrial Co., Ltd. Method of preparing a pharmaceutical composition comprising fermented ginseng
WO2005023281A1 (en) * 2003-09-06 2005-03-17 Oscotec Inc. Composition comprising notoginseng radix extract for preventing and treating arthritis as an effective ingredient
US8927033B2 (en) 2009-12-21 2015-01-06 Lion Corporation Hyperlipemia-ameliorating agent, anemia-ameliorating composition, uric-acid-level-reducing composition, and food or beverage

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GB2056855B (en) 1983-06-29
DE3029363A1 (de) 1981-03-26
JPS6352013B2 (enrdf_load_stackoverflow) 1988-10-17
CH650153A5 (de) 1985-07-15
JPS5626818A (en) 1981-03-16
GB2056855A (en) 1981-03-25

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